“How awkward!”

You were coming out of the elevator and said "goodbye" to one of your coworkers. But then you both started walking in the same direction. It's strange to say "goodbye" before you actually leave someone, so it makes you uncomfortable. You want to make a joke about it to make yourselves more comfortable. You say this.

How awkward!

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How (adjective)!

The phrase "How ___!" basically means "This is very ___!" For example, if something is really soft, you can say:

How soft!

And if a friend tells you about something annoying, you can say:

How annoying!

The phrase "How ___!" is used mostly in spoken English, not written.

(an) awkward (situation)

An "awkward" situation is uncomfortable because you don't know how to act. In the example at top, the speaker feels awkward because he has already said "goodbye" but now they have to walk with each other. So he doesn't know if he needs to say "goodbye" again, or just stop talking to the coworker.

Some other examples of "awkward" situations are:

  • You're on a first date with someone and you run out of things to talk about.
  • You're giving a presentation, and the person who introduces you calls you by the wrong name.
  • You find out that your teenage son has been having sex, and you have to talk to him about it.

Of course, you don't directly say "This is awkward" in all of those situations. But you would use the word "awkward" to describe the situation when you're telling another person about it.